[quote name='ryosnk']Check out
Navy Pier,
Woodfiled mall,
Sears tower, and other great sites.[/quote]
Here are a few areas/places I'd recommend:
Couscous. Killer middle eastern restaurant in the Little Italy neighborhood, which is a little bit southwest of the loop. You can get to it from downtown by taking the Pink Line to Polk and walking a couple blocks. Get the falafel plate appetizer.
Wicker Park. Get on the O'Hare "leg" of the Blue Line and get off at Damen. That will bring you to the three-way intersection of Damen, Milwaukee and North. Places you might want to look up are
Reckless Records,
Myopic Books and
Odd Obsession Movies, although you'd probably find interesting stuff around there just walking in any direction from that intersection. Within reason, of course.
Lincoln Square. Take the Brown Line to Western and explore. Lots of cool shops on Lincoln, which is a diagonal street about a half-block east of where the train will spit you out.
Chinatown. Chicago's Chinatown is deceptively small, but surprisingly legit. Real southern Chinese culture, and not too much tourist crap. I'm a fan of the
Ten Ren tea shop. Their cheapo boxed teas are sort of lame but they sell bulk teas by the ounce, ranging from low-grade ($20 a pound or so) to primo shit ($~150 a pound). Get some decent quality jasmine or oolong. But stay away from the green... green tea is a Japanese thing. Chinese green tea is a waste of time.
Lakeview/Belmont Area. Take the Red Line to Belmont and head east (right turn out of the station. Walk along Belmont, stopping at all the places that catch your eye. After a block or two you'll be at Belmont & Clark. Explore Clark for a few blocks in either direction, and eventually make your way back to Belmont and continue heading east. After a few more blocks you'll get to Belmont & Broadway, and from there you can take a right turn at Broadway and check out some more good stuff, including another Reckless Records location. If you're hungry you can go down Broadway to
Bamee Noodle Shop, probably my favorite Thai restaurant in the city. Get the Rama Broccoli, unless you're some sort of freak who doesn't like broccoli.
Museum of Science & Industry. If you're going to hit a tourist trap, hit this one. Kickass museum. Google it... their site should list ways to get there, including a bus route that goes straight from downtown to the museum.
Pizzeria Uno/Pizzeria Due. In recent years, a shitty restaurant called Uno Chicago Grill has started cropping up around the country. Ignore that. You have to go to one of the originals.
Uno and
Due are basically the same restaurant split up into 2 locations around the corner from each other. They're both right by the Grand stop on the Red Line. You'll want to shoot yourself in the head after eating this pizza, when you realize that you'll never be able to truly enjoy pizza in your city ever again.
Don't go to Woodfield Mall. Don't go to Westfield Mall. Don't to go any damn shopping malls. They look the same in every city across the country.
Also, DO NOT rent a car in Chicago unless you're a millionaire. If you do, and you plan on parking it downtown, plan on parking in a garage that charges $15...
for the first 20 minutes. Your best bet would be to do some research and find the best price you can on a hotel that's located as close to the loop as possible. It will be an expensive hotel, but you can pretty much go to any location in the city from the loop via train, and going carless would more than make up for the hotel price. Besides, it's nice to be able to start sightseeing from the moment you step out of the hotel door. The only thing I'd say about that is don't stay at the Congress Plaza Hotel. Their employees have been picketing for about four years. Don't support them.
